


Letting Him Down

by Ghara2



Category: Gravity Falls
Genre: 69 (Sex Position), Adult Dipper Pines, Anal Sex, BillDip, Christmas Smut, Dry Orgasm, Handcuffs, Human Bill Cipher, Human!Bill, M/M, Master/Slave, Orgasm Delay/Denial, Overstimulation, Riding, Seduction, a bit of aftercare, handjob, love egg
Language: English
Status: Completed
Published: 2018-01-24
Updated: 2018-01-24
Packaged: 2019-03-08 23:42:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,764
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13469076
Author URL: https://archiveofourown.org/users/Ghara2/pseuds/Ghara2
Summary: Dipper breaks a promise, but he does try to do what he said he would a day too late.





	Letting Him Down

**Author's Note:**

> I am one month late but I finally finished this oneshot!! I hope you guys enjoy! I was aiming to post this right on December 25 12:00 AM on 2017, but our finals for software development literally held me back for a whole month, so here's this Christmas smut oneshot a month later! Sorry it took so long ;;
> 
> For tradition purposes, I'm just gonna say: Sorry Jesus Christ

It was the night after Christmas. It was cold outside—which was a given since it was snowing, but it was, of course, slightly warmer when the sun was up and the wind blowing less harshly in the day—but no amount of precipitation would be enough to prevent a demon from simply teleporting to the door of his boyfriend’s house. Why would it? Sure, snow might fall onto his tuxedo—or more likely, his lustrous golden hair that stood out from the white surroundings—which would be unfortunate, but tolerable, and most certainly worth it. He could’ve teleported into the house rather than outside the front door, but he’d like to see how willing his property was to serve him after two consecutive days with separate parties for the same damn holiday.

The demon knocked on the door thrice after adjusting his bowtie. Right away, the excited, rather frantic and nervous brunet, whom he definitely loved more than any entity in the entire multiverse and most definitely owned, opened the door and greeted him with, “Hey, Bill. I missed you, uh…c-come in, please.”

“You know very well that we were together yesterday and even the day before that. I don’t think you actually missed me, but sure, I’ll come in.”

Bill walked into the house and waited as Dipper closed the door. He stood in place, hands on his hips and his expression still insouciant. Mildly vexed, to be more accurate. Dipper knew why he was acting so displeased. He _is_ the cause of that displeasure, after all, and he knew very well that he had to make it up to Bill, which is why he hastily yet carefully patted the snow off the taller man’s tuxedo.

“Uh…y-you actually have some snow on your hair too. Do you want me to go get a chair, or…? I-I mean, I can _reach_ it, but…”

“No need. Here you go, short stuff.”

Bill bent down and let the brunet tidy his head up. He was much taller than Dipper, which is why it would be a little difficult for Dipper to get the snow off the top of his head carefully and precisely. Their height difference was ridiculous, but that was because Bill decided to make his human form more than tall enough to be able to use his Pine Tree as an armrest. He certainly stood out among humans, but it was worth it; annoying Dipper was always fun, and the opinions of mere humans—Dipper wasn’t a mere human to him though—didn’t matter to him, nor could they affect him in any way at all. Well, Dipper didn’t actually get annoyed by being used as an armrest anymore, but he still acted like it sometimes, and it was also always fun to play with him anyway.

“All done. Y-Your hair’s snow-free now. Do you want me to do something else before I take you to your seat? Like uh, give you a kiss or hug you, maybe?” he offered.

“No thank you, Pine Tree. Go on, show me what you’ve prepared,” Bill said as he stood straight.

“O-Okay.”

“Did you really think I don’t want you anymore? I would never give away what I own,” Bill remarked, walking to the romantic candle-lit table.

“N-No, but…you’re mad, and if I continue to displease you, you might get sick of me and decide to leave me. You…you know I don’t want that. B-But hey, tonight’s about what _you_ want, so—“

“I’m never going to leave you, so stop your adorable worrying and serve me.”

“O-Okay. Oh, uh, wait!” Dipper trotted to the table he set and pulled out a chair for the taller man. “Here, Bill.”

Bill sat down and watched as the brunet did the same across him. There was no one to pull his chair though, of course. It was a little pitiful, considering the golden-haired man would usually take care of that, but because of what Dipper _didn’t_ do, he wasn’t going to treat him specially until he somehow makes up for it.

“So, what have you prepared for tonight?”

Bill placed his hands on the table, clasped together specifically to strike Dipper with the sense of his superiority and make him even more nervous.

“W-Well, besides myself, I made us some coffee. It’s still in the coffee maker, so it’s still nice and hot—like you—and I can give it to you just how you like it…likehowyoudome. I also bought your favorite dark chocolates and sliced them so you don’t have to eat them from the bar, prepared a bowl of cherries, and a jar of honey in case you uh…want to add it to anything. I-If you want red wine instead of coffee though, it’s okay, I have three bottles.”

“I’d prefer that you make me a cup of coffee. Wouldn’t want to fuck you in my drunken stupor.”

“Right…of course you don’t want to do me. I’m sorry. I’ll go get our coffee.”

“Hey, we just sat down. Don’t leave the table just yet.”

“Oh…well, it’s our only drink unless you want me to get some water too. Then again, it’s not on the table either, so…no drinks yet. You okay with that?”

“Yes.”

“Okay, if you say so, um…here. Would you take my cherry?” Dipper said, holding up the said fruit as closely as he could to the demon.

Bill looked at Dipper, whose cheeks—and cute little nose—were much redder than usual. The brunet was clearly trying to seduce him, which was expected, unfair, and a desperate action. However, as much as Bill wanted to make Dipper suffer like he did, he was successfully seduced. Dipper was adorable, especially when he would beg or talk dirty, both of which he basically just did, and even in a tuxedo, he still looked so submissive. Now, Bill wouldn’t completely give in, but he could indulge himself a little.

Whilst taking the cherry, the demon made sure to graze the brunet’s fingers with his own. Dipper smiled as he felt Bill’s skin on his own. It was a little surprising that Bill decided to tease him in the first place, but it was really nice of him, and it also meant that he still had a chance.

“Pretty sure I already took your cherry about a year ago.” Bill smirked, then parted his lips and stuck out a bit of his tongue. He placed the cherry on his tongue and, as he retracted it, he pressed the juicy little fruit between his lips. He made sure to look into Dipper’s lovely brown irises as he sucked the cherry into his mouth, and once it was fully inside, he leaned forward and rested his chin on his hand, inviting Dipper to pull out its stem. He then placed it on his plate and watched as the taller man ate the cherry.

“Do you like it?” he asked after Bill swallowed.

“Depends on which cherry you’re talking about. If you’re talking about _your_ perfect ‘cherry,’ I didn’t like fucking you for the very first time I absolutely loved it. If you’re talking about the little red fruit of temptation I just ate, it was quite delicious.”

“Oh…g-good,” Dipper remarked, referring to the first ‘cherry’ he mentioned. “I’ll get our coffee now, if you don’t mind.”

“Alright. Eager to please me with one of my favorite beverages, I see.”

Dipper stood up and walked to the counter he’d set his coffee maker on. He poured the hot drink into Bill’s special mug, then his own. He mixed in the additives they preferred in their coffee—extra carefully with Bill’s—and once he was done, he brought their mugs to the table and set them down.

“Here you go,” Dipper said as he sat on his chair.

“Thank you. Now, you know this is how I like my coffee, which means I don’t want anything else added to it unless you somehow messed it up, which I think is highly unlikely. Better not let me down. _Again_. Anyway, that said, would _you_ like some, honey?”

“…Did you just call m—nevermind, it’s a cute pun. Anyway, I guess it was stupid of me to prepare honey; you don’t need or want it and neither do I. I mean, I don’t want its taste mixed with my coffee…I want it directly in my mouth,” Dipper said, trying to sound seductive by putting some growl into his last sentence.

Bill chuckled at Dipper’s attempt to seduce him yet again. It was enticing, certainly, but it was also pretty silly. “Alright, here’s the honey, _Dipper_ ,” he replied as he held the honey dipper between his fingers.

The brunet laughed at the charming pun the golden-haired man came up with for his name. “I like that one. Anyway, here I go.”

Dipper leaned forward, and similarly to Bill, he rested his head on his fists. He then opened his mouth and stuck out his tongue as he gazed into the demon’s eyes.

Bill licked his lips, tricking Dipper into thinking he was successfully seduced. Dipper was cute, but that’s just how he always was, and though he’d rather thrust his dick into that mouth than put honey in it, he wasn’t growing impatient or anything like that. Nevertheless, he lifted the honey dipper, rotated it a bit so honey wouldn’t drip onto the table, then held it just above the brunet’s mouth. They both waited as the honey slowly dripped onto his Pine Tree’s tongue.

Dipper closed his mouth and softly moaned as a little leftover honey got onto his lips and chin, just to seduce Bill even more. “Bill, you got it all over my mouth…” he playfully whined after swallowing the sweet, viscous liquid.

“You’re trying too hard, Pine Tree. Clean it up yourself and maybe I’ll reward you,” Bill said as he took a piece of chocolate.

“Okay, okay, sorry.” Dipper quickly takes the napkin he’d placed on the table and used it to wipe the honey off him. He then put it back where it was, and looked up to see his lover gazing at him with a piece of chocolate pressed between his lips. Dipper furrowed his brows in confusion, but immediately understood what Bill was telling him to do once he saw him lean forward.

Dipper learned closer to the taller man and carefully pressed his lips onto Bill’s, letting Bill push the chocolate into his mouth while kissing him. For just a split second, the brunet felt the demon’s tongue. He wanted more, but Bill pulled out once the chocolate was in his mouth, and he probably wouldn’t let him have the pleasure of a French kiss just yet.

“Good chocolate, huh?” the golden-haired man said, smirking.

“I mean, yeah, of course; I did buy them for you. You’re better though…”

“Desperate, aren’t you, Pine Tree?” Bill chuckled, but clearly he was being wry. “I’d call you Pineslut, but you weren’t acting like that for the past few days. What a shame. It really would suit you right now; I know what you’re doing. All the food you’ve prepared, and even the coffee—they’re all known to be aphrodisiacs. _Now_ you want me to fuck you? How selfish.”

“Look, I’m sorry. I’m really sorry! I was just so tired after every party; I I would’ve passed out while we were having sex if I let you do me…”

“Well, after _one_ party, you knew you’d get tired if you exerted yourself just as much at the _next_ party, right? You’re a smart little sapling, I know you knew that.” Bill sighs, sounding more disappointed than angry. “You know how important deals are to me, Pine Tree. You promised you’d have sex with me or before Christmas. You were so confident; you even said you’d ride me. I was so excited, but guess what? It’s the day _after_ Christmas.”

“I know, I’m sorry…you were only expecting because I made you. I really am trying to make it up to you tonight, but…will you let me? Please? I’ll do anything you want tonight, I…I promise, though I’ll make this a deal sealed with a handshake if you want.”

The demon stared at the brunet for a while. He was skeptical, but he couldn’t say no to that pleading face. Those damn unintentional puppy eyes were just irresistible, and though Bill knew he’d give into them even if Dipper used that trick for something he didn’t like, he didn’t mind them at the moment, knowing that Dipper was being genuine. It wasn’t like he couldn’t see into his Pine Tree’s heart, and in it were remorse and desire.

Of course, he still wasn’t going to let Dipper off that easy. Pardoning his actions were more than enough.

“No need to make it a deal, Pine Tree, I’ll just see how well you’ll keep your promise, assuming you do keep it. Wait for me in the bedroom, and start stripping once you’re in there.”

“But the dishes, and your coffee…I-I mean, I’ll do what you say, but—“

“I’ll handle it. Just go.”

“Okay…um, thanks for sparing me the trouble.”

“Yeah, no problem.”

Dipper wanted to give Bill a hug and a kiss, but he’d be doing that soon anyway, so he just started walking to his room like he was told to. He glanced at the golden-haired man a few times along the way though. He smiled to himself, touched by how Bill was being nice despite him having broken a promise. Sure, Bill would definitely be rough with him later on, but he wouldn’t go too far.

It didn’t take long for the brunet to reach his room and get inside. He took off his shoes and socks, then began to unbutton his tuxedo. He dropped it on the ground rather than use a hanger. The tuxedo was, of course, expensive, but he didn’t have the time to store it properly; Bill likely wanted him to be naked by the time he gets into the room as well. Dipper then undid his button-up and simply let it slide off his arms after he took off his tie, leaving his entire torso bare. With those on the floor as well, he started taking off his pants.

Before Dipper could take off his underwear, Bill entered the room.

“Bill! I-I didn’t realize that…I mean, sorry that I haven’t taken everything off for you yet. I’ll get to that right now.”

“Go ahead, you don’t have to rush just yet,” the taller man replied as he took off his tuxedo, and following that, his shoes and socks.

Dipper quickly took off his boxer briefs, more eager to please Bill than afraid to displease him. Leaving those on the floor as well, he sat on the bed, about to lie down and let the demon do whatever he wanted; it was how they usually did things. However, it seemed that they were apparently going to do things differently this time, which wasn’t exactly a surprise; just something Dipper didn’t expect to be the case.

“You don’t get to stay on the bed just yet, Pine Tree. On the floor you go, against the wall, right now,” Bill ordered.

“Yes, Bill…or would you prefer ‘Master’ this time?” the brunet asked as he stood up.

“I’d like to hear you scream my name tonight.”

“Okay.”

Dipper sat on the floor and against the wall, just like Bill told him to. He spread his legs as well, knowing he’d end up doing it at some point. Meanwhile, Bill was going through the contents of a previously tied gift box he’d put in the closet before. He never put a gift tag on it, which left the brunet curious about it since he first saw it. That was the point, actually—the gift was for Dipper. An extra gift, that is.

The golden-haired man took out a bottle of lube and a love egg along with its remote from the box. He placed them near Dipper, on the cloth they were wrapped in to keep them clean. Dipper simply stared at them and imagined what he’d be doing with it, but just for a brief moment; he directed his attention back to Bill when he walked back to their closet and opened the much bigger box they stored all their kinky stuff in.

Bill took out the handcuffs he’d always used on Dipper. He was tempted to take the blindfold as well, but he decided he wasn’t going to use it later on. It’d be fun, but it’d interfere with some of his plans.

“…What are you gonna do to me?” Dipper asked, sounding curious and seductive, rather than afraid.

Dipper knew Bill loved hearing and answering that question; it always made him feel more powerful, which is what any demon would want, really—dominion over souls. Of course, he already knew that he owned every part of Dipper, but that didn’t mean a reminder every now and then wasn’t welcome.

“Other than restraining you with these and watching you, nothing just yet. _You’ll_ be doing something if you want me though,” Bill answered as he walked back to his Pine Tree.

“What is it?”

“Hands behind your back.”

The brunet did as he was told, and while Bill put the handcuffs on Dipper’s wrists, he nonchalantly continued with his answer. “You’ll have to get yourself hard with the love egg I got just for you. Of course, I’ll be the one to slip this into you; you’ll do the rest, and I don’t mean you have to _just_ get yourself hard.”

“I…What else can I do without my hands?”

“Well, it’s more like you have to _not_ do something, actually, so this should be easy for you.” Bill chuckled lowly. “I get to control the remote, and you’re not allowed to cum. Easy enough, right? It’s a small price for something so much greater.”

“I’ll do my best…” Dipper sounded a little nervous; he knew what would happen if he couldn’t stop himself.

Bill smirked. “Oh, and I’m allowed to touch you if I want to, but you’re not allowed to do anything to me. Understood? No kisses, no leaning on me, nothing unless I say so.”

“Yes, Bill,” the brunet replied, looking the demon in the eye.

“Good. Safeword?”

“Mortal.”

“Alright. You’ll know when to raise your legs.”

Bill took the bottle of lube and poured some of its contents onto his free hand’s index and middle fingers. He then closed the cap, set the bottle down, and waited as Dipper adjusted his position so he could raise his legs and keep his balance.

Bill would’ve praised Dipper like he usually did, being perfectly aware of his Pine Tree’s little praise kink, but this was a different night. He didn’t want to let Dipper feel good about himself just yet. After all, all he’d done so far was lift his legs anyway, which isn’t exactly praiseworthy. Giving rewards for a-little-above-mediocre actions would only make Bill seem kind and lenient, which he was not. Kind occasionally, but not lenient.

Without saying anything, Bill pressed his lubricated fingers against Dipper’s ass, making the brunet softly gasp at the sudden cold sensation. The demon certainly enjoyed that reaction, and he couldn’t help but lick his lips as he lightly rubbed his Pine Tree’s hole. Dipper whimpered, definitely feeling good, but wanting more than just teasing. He wanted to move and entice Bill to slide his fingers into him already, but he couldn’t.

“Stay in that position.” Bill picked up the love egg and coated it in lube as well. He wasn’t in a hurry, but he did it rather quickly; he was excited for the show to start, after all.

Bill slowly inserted the small vibrator into Dipper’s ass, making him moan. Of course, the little girth and length it had wasn’t nearly enough to satisfy his need to be filled, but he moaned a little louder anyway when he felt it touch his prostate. It didn’t give him a _huge_ jolt of pleasure—not yet, anyway—but it still felt good. He could imagine what was coming though, and he was both excited and a little scared.

“You can move if you want to now, but remember, you can’t cum,” the demon said as he got up and sat on the bed’s edge.

“Y-Yes, Bill. And thank y—ahh!” Dipper yelped as he felt the sudden stimulation in one of his most sensitive spots.

“You didn’t expect a warning, did you, Pine Tree?” Bill asked with a smirk and the remote in hand.

“N-Nnno, o-of course not…”

“Hm…didn’t seem like it though.”

“I really didn’t! Th-The…The vibrator just…ah…feels really good…”

“Alright. It’s only on the lowest setting right now, though you seem to be enjoying a lot already.”

“Well, I…mm…I’m not surprised you managed to…mm…stick it right onto my g-spot.”

“Having fucked you more times than you can keep track of has its perks.”

“Y-Yeah…not a lot of people can do it immediately like you did, you know…?”

“Of course I know. Now, seeing as you’re getting hard, how’s about I turn this up, say…two levels? Three levels? There’s twelve in total, Pine Tree, and you’re going to have to get through them all before you get to have me in your cute little ass again.”

“T-Twelve?! I-I—“

“Three more levels it is.”

Bill pressed the button thrice without pausing, making Dipper yelp again and continue to helplessly moan and squirm in the same position he was in when Bill put the vibrator in him.

“B-Bill…I…I-I don’t know if I…i-if I can…ngh…hold out u-until the twelfth level…p-please…”

“Giving up already? How disappointing. Really Pine Tree, you’re letting me down again?”

“N-No, I-I…well…I…I can’t stop myself from cumming before the…l-last level, but m-maybe I can do something e—ah…else for you…please? I-I—AH!”

The golden-haired man pressed the button once more, intending to make Pine Tree remember his place. He doesn’t get to decide what they do during sex unless he begs prettily enough, or if they’d agreed on something prior, so Bill had to punish him at least a little for that nerve of his to ask for something that would contradict the order he was given.

“Bill, p-please…t-this vibrator you got’s really intense…I-I can’t…p-please, I need you…b-but I can’t…I-I’ll do anything else, just please…I-I’m sorry I mm—made you wait, b-but I really need you to…f-fuck me…and…m-make me cum…”

Dipper slowly got up and on his knees, grunting and struggling to not pleasure himself more than he already was as he did so. He then shakily shimmied to Bill, still on his knees, and rested his head on his master’s thigh. “I-I’m sorry I-I’m technically touching you, but please…mmm…”

Bill stared back at the brunet, who was currently between his legs and fidgeting. Dipper’s lips were slightly parted, and between them came out audible shallow breaths and soft mewls. Having his seductive little bitch so much closer to his crotch made Bill’s dick grow harder, which may have inclined him to give in, but he certainly didn’t mind at all.

Before giving the brunet an answer, the golden-haired man ran his fingers through Dipper’s hair. He enjoyed the cute, needy noises his Pine Tree was making as he did so, especially when he would tug on his fluffy brown locks.

“S-So…w-what do you say…?” Dipper asked after quite a while, lustfully gazing at the tent in Bill’s pants.

The demon smirked and chuckled. “Alright.”

Bill lowered the intensity of the love egg by two levels, leaving it at its third. Dipper sighed, still in pleasure, but also in a bit of relief that he wasn’t going to cum just yet. He could swear love eggs aren’t supposed to be strong at all at their first few intensity levels, but he wouldn’t have known firsthand. He didn’t mind too much though.

“I’m not taking that out of you yet, but I suppose you can have a little taste of me…well, a lot, maybe, but I wonder what you’ll be focused on more.”

The demon began to take off his button-up. The thought that he might be indulging his Pine Tree a little too soon did strike him, but he decided it’ll be fine as long as Dipper still suffers.

“Get off me for just a few moments, Pine Tree. I have to take these off.”

“Yes, Bill.”

Dipper lifted his head and backed up a little to give the taller man some space. He watched Bill toss his button-up to the pile of clothing after he stood up, then strip off his pants, leaving him in nothing but his underwear, which made the brunet want to uncover that bulge even more.

“Like what you see?” Bill teased.

“Yes,” Dipper replied, looking his master in the eye.

“You want it?”

“Mmm…yeah…I-I _need_ it…”

“Good, now you’re sounding like my Pineslut.”

Bill finally took off his boxer briefs, though he was teasingly slow. He let Dipper lick his lips at the sight of the tip of his cock, admired the slightly louder and breathier moans as he revealed more and more of its shaft, and once it was fully exposed, he tossed his underwear to the pile.

“You can get on the bed with me, but keep your ass right in front of my face while you suck me off. Otherwise, no dick for you later. You wouldn’t want that now, would you?”

“N-No, o-of course not…”

“Good.”

The demon lay on the bed and watched the brunet climb onto him and position himself while struggling with the stimulation from the love egg that was still inside of him. Again, he was shorter than Bill, so it was his ass that ended up right in front of Bill’s face, rather than his cock; he didn’t have to move a little forward for that.

“M-May I…?” Dipper asked, his breath already making Bill’s dick twitch.

“Go ahead. Just don’t cum before I even fuck you in the ass; that would be _very_ impolite of you.”

“I-I’ll do my best…”

“What, you can’t promise me that you’ll obey my orders?”

“I’m sorry, I-I can’t…y-you might make me feel too good…”

“Alright, I suppose that’s one way to put it, but I’ll make sure you’ll be feeling this tomorrow and days to come. Now start.”

Dipper slowly took Bill’s length into his mouth. Bill sighed, relishing in the warmth gradually enveloping his dick, and let out a moan in unison with Dipper—though the sound he made was choked, of course—as he felt it hit the back of the brunet’s throat.

“I know you can go deeper—Mm…fuck, that’s my Pineslut.”

While Dipper was busy deepthroating, Bill gave one of his Pine Tree’s butt cheeks a harsh slap that resounded in the room. He then grabbed onto the brunet’s hips as he grunted because of Dipper’s yelp getting muffled by his dick, and dug his nails into them. He then clawed on them, gave the brunet’s other butt cheek a slap as well, and dug his nails into Dipper’s hips again.

Rather than making more scratch marks, the demon ran his tongue over Dipper’s soft perineum. His Pine Tree wriggled his ass in response, instinctively pushing it onto Bill’s face as he struggled to lift his head so he could actually speak.

Just as he pulled away enough to get his master’s cock out of his mouth, Bill nibbled on his taint. Bill did it lightly—for his standards, that is—but it was enough to make Dipper scream his name already; so early in their long night, and it was especially loud without anything to muffle him at that very moment.

The golden-haired man chuckled. “I haven’t even fucked you yet, Pineslut. Will you be screaming even louder later? Your voice is always music to my ears, so how’s about you sing for me more, hm?”

“Mm…I-I…haah…m-maybe, but…B-Bill…I c-can’t take m-much more…a-ah…I-I’m gonna cum…b-but I don’t want to y-yet…mh…m-maybe if you…take the vah…vibrator out I…h…haah…!”

Bill began to slowly pull out the love egg, but right when he felt it was about to come out of Dipper’s sphincter, he let go of the string, letting his Pine Tree involuntarily suck the sex toy right back in. He repeated those actions, and Dipper could only keep whining, “Bill, no…! P-Please, no…!” between his moans.

“G-Gonna cum…s-stop…!” he pleaded after a while, his head resting on Bill’s thigh, just beside his dick.

Bill couldn’t see his Pine Tree’s face at the moment, but he could tell by just his voice that he was melting in pleasure, though he was also trying to resist it and was failing miserably.

Knowing Dipper wouldn’t be able to hold back, Bill but on his buttcheek, sending the brunet over the edge and making him scream his master’s name. His thick, white load spurted all over Bill’s stomach, and with Bill eagerly sucking on his butt cheek and the vibrator still on, he was still trembling and loudly moaning.

“I-I’m sorry…for m-making a-a mess on you…! Ah…a-and disobeying you…”

The demon pulled away after a few moments and gazed at the huge hickey he just made, which was overlapping part of the slap mark from earlier.

“I think you know an apology will never be enough.” Bill snapped his fingers, conjuring a collar with a chain leash attached to it around his Pine Tree’s neck. “Keep sucking, Pine Tree. We’re not done here,” he commanded as he tugged on the leash, eliciting a startled, wanton moan from Dipper.

“O-Okay…” The brunet struggled to lift himself a little. Though he was feeling a lot weaker from just having an orgasm and still being stimulated, he did it for Bill, even without being able to use his arms.

Once he’d lifted himself enough, he took Bill’s length back into his mouth. He did so a lot quicker; he basically let his head just drop, and he gagged as the girth thrusted right into his throat, more so when his master tugged on the leash. Bill continued to cover his Pine Tree’s ass with love bites, savoring his taste each time he would lick and suck, and resist the urge to break Dipper’s soft skin with every bite; he was saving that for another body part, if possible.

A harsh tug on the leash would come whenever Bill would sink his teeth into Dipper’s flesh, but it would startle the brunet and make him choke every time anyway. It always felt good though, and he would hope that Bill would cum when he’d thrust the demon’s dick into his throat. He wanted to feel his master’s warm, viscous fluids coat his throat and slowly flow down as he swallows, but at the same time, he wanted Bill to fill him with his seed as he fucks him in the ass.

Once the golden-haired man decided that Dipper’s but cheeks were clawed, bitten, sucked on, and slapped enough to sting upon more skin contact, he gently traced little circles on the brunet’s hips with his thumbs—a sharp but nice contrast to his actions so far.

“Pine Tree, want me to fuck you now, hm?” he asked as he slid one of his hands towards Dipper’s cock.

While the brunet was trying to lift himself again so he could speak, the demon wrapped his fingers around Dipper’s shaft and starting stroking it up and down, with a gradual twist as his hand went towards its tip and its base, making it harder for Dipper to focus on what he was doing so he could give his master a proper answer. The fact that Bill was teasingly slow didn’t help, either.

“I know you love it when I touch you, Pine Tree, but give me your answer,” Bill teased, clearly knowing what he was doing.

Dipper coughed a few times once his mouth was finally free, making the demon smirk. “Y-Yes…please…I-I…I don’t…I’m close again, a-and I—mh—mmm…!”

Bringing Dipper closer to another orgasm, the golden-haired man started to slowly pull the love egg out while still giving him a little handjob, but this time, he actually did it all the way, and while teasing the brunet, too.

“You were saying?” he asked as he set the sex toy aside.

“Ahh…I-I don’t want to…mm…cum without you inside of me ah…again…”

“Good, at least you’re holding it in this time. You can ride me now; ride me until I’m satisfied with you for the night.”

“Yes, Bill…”

With that, Bill let go of Dipper’s cock and watched the brunet weakly lift himself. He could barely lift his legs, let alone kneel without his buttocks resting on the golden-haired man; his knees were shaking, and he trembled as he positioned himself very carefully.

Dipper managed to kneel facing Bill after a while, but he couldn’t ride him just yet. Not with those handcuffs on, anyway. “Um…Bill, c-can you…maybe help me put it in…?” he asked.

Bill chuckled. “Of course, Pineslut. I’ll lube it up for you, too.”

The demon held the leash in one hand, and with the other, he lifted the bottle of lube with a little help from his magic. He squeezed some of its contents onto his cock, then put it back where he’d set it down earlier, and proceeded to actually use his hand to spread the lube all over his dick.

“Alright, you can continue now,” Bill said, holding his cock up.

“Thank you…”

“You’re welcome, Pineslut.”

Dipper moved a little so his entrance was pressing against the tip of Bill’s cock. He’d rub against it a few times if he had his hands free and able to help him balance himself, but they were still cuffed behind his back, so he skipped that party. Slowly—though clearly eagerly—he sank onto Bill’s erection until every last inch of it was inside of him. He let out a loud, sultry moan, finally experiencing the satisfaction of his master’s dick stretching out his insides and filling him with the warmth he loved so much.

The demon smirked, very much pleased and amused with not only that beautiful sound his Pine Tree just made, but also his face. Currently, he was melting in pleasure; his half-lidded eyes were clouded with lust, his cheeks were crimson, and he was slightly sticking his tongue out. His back was arched, further exposing the light sheen of sweat on his body, as well as his cute little perked up nipples. He was an absolutely beautiful sight, and Bill relished the fact that no other being in the multiverse was allowed to or even could see Dipper like this.

The brunet shakily raised himself, then let himself drop back onto Bill. He let out another loud moan amongst his softer whimpers as his master’s cock quickly rubbed against his prostate and slammed deep into him, though the sound he was making got choked by Bill tugging on the leash.

Dipper repeated those actions for a while, eliciting a groan and a tug from Bill each time. He was painfully slow though; he could feel himself get so much closer to another release, especially with the stinging sensation from his defiled butt cheeks harshly coming into contact with Bill’s hips, but the speed he was going at just wasn’t enough, and he was too weak to go any faster.

“Bill…” he whined.

“Yes, Pine Tree?”

“I…I-I need you to fuck me faster…please…”

“I thought you’d be riding me to your heart’s content tonight, Pine Tree. Letting me down again tonight? What a shame…you feel really good, you know. I’d hate to let you go…”

“N-No, Bill, please! I-I…I-I’m really weak because of the things you’ve done to me so far…I-I can’t go any faster, but I want to…I-I need you so bad…please…d-don’t leave me, I-I’m sorry…I…mm…”

Tears welled up in his eyes in desperation. He whimpered as he felt Bill’s cock twitch inside of him, which was a good sign, but he still needed his master’s answer.

Bill was definitely turned on by Dipper begging so prettily. He was a bit close to release himself, but he wasn’t going to say that. He’ll give in to his Pine Tree’s request though; he did make Dipper cum without even actually fucking him and continued to pleasure him afterwards, after all.

“Alright, alright, I’ll fuck you faster. I won’t stop until I fill you up; sound good?”

“Yeah, _really_ good. Thank you, I-I really need—AH!”

Bill grabbed Dipper’s hips, lifted him, and slammed him back onto his hips while thrusting them upwards without hesitation, making the brunet yelp and himself groan. He didn’t mind the fact that doing so meant not being able to tug on the leash anymore; this was definitely worth it.

“I know what you want and need and I’ll be giving it to you, so instead of talking, let me hear your beautiful screams, Pine Tree.”

With that, Bill thrusted into the brunet after lifting and pulling him back down yet again. He repeated those actions, moaning as Dipper’s warm, slick insides engulfed his cock and tightened a little when he’d ram as deep as he could into him.

Dipper was continuously letting out a slew of moans and screams of his master’s name that became less and less coherent the more Bill fucked him. Those noises, along with those that came out of Bill’s mouth, and the sound of their skin slapping against each other filled the room. With the immense pleasure of Bill’s cock rubbing against his prostate and slamming deep into him and the pain of the marks the demon made on his ass coming into harsh contact with Bill’s skin amplifying his arousal, it didn’t take long at all for him to get sent over the edge once again.

He screamed in between loud, desperate gasps, his eyes wide open and his mouth agape with his tongue out in euphoria as he spurted out all the semen that was left in him. His insides clenched Bill’s throbbing cock, bringing his master closer to his orgasm as well.

Bill was too far gone to even talk to Dipper as he continued to fuck him roughly and make him scream. After a few more thrusts, Bill grunted loudly as he buried himself as deep as he could into his Pine Tree and filled his insides with his viscous fluids.

As Dipper felt his master’s cock twitch and spew out his seed lots of times, he felt another surge of pleasure take over him, and he uncontrollably let out even more screams, though some of them turned into whimpers along the way due to his lack of breath. Nothing came out of his cum dripping cock anymore, but he still felt just as overwhelmed as he did in his other orgasms.

Dipper couldn’t think straight nor see straight at the moment. He stayed in the position he was in when he came, and occasionally twitched as he took loud, deep breaths. He was looking nowhere in particular and his head was in the clouds. He could feel some of Bill’s cum drip out of his hole, but being deprived of oxygen, he could only whimper.

Bill barely moved at all either, panting as well, although definitely less desperately than his Pine Tree. His grip on the brunet’s hips was much looser, and not wanting to do much just yet, he gazed at Dipper, who clearly couldn’t take any more for the night.

Once he felt relaxed enough, he let go of Dipper momentarily to brace his elbows against the bed. He slowly sat up, then he snapped his fingers, making the collar, leash, and handcuffs that he’d put on his Pine Tree disappear.

“I’ll take it out now, alright?” he said, returning his hands to Dipper’s hips.

“O…Okay…” Dipper replied, still breathing heavily and barely able to speak.

Bill tightened his grip a little, then proceeded to slowly and carefully lift him, making his Pine Tree mewl as his cock gradually slid out of him. More of his cum spilled out of Dipper, but he didn’t care; he was more than satisfied, and clearly, so was Dipper.

He placed the brunet on his lap once his cock was fully out of Dipper’s body. He gently wrapped his arms around his Pine Tree’s waist and pulled him into a warm embrace. Dipper kept his hands where they were, but only for a few moments; he seemed to have finally realized that his hands were actually freed, and with that, he weakly but eagerly hugged Bill back.

“Cold…” Dipper whined, unable to speak very much just yet, but already missing Bill’s warmth inside of his body.

“Aw, Pine Tree…” The golden-haired man planted a small kiss on the brunet’s neck, then lay back down, taking Dipper with him. “You’d pass out if I fucked you more. You know that, don’t you?” he cooed.

“Yeah…but…”

“Breathe, Pine Tree. Stay awake for a little longer; I want to pamper you.”

With that, Dipper focused on gasping for air. His breaths grew less audible, and Bill languidly stroked his back as he tried to fully come back to his senses, but somewhere along the way, tears started to fall from his eyes yet again. He wasn’t sure whether he began to cry again because of how lovingly Bill was currently testing him after all that rough treatment, or because he was overwhelmed by everything he’d gone through throughout the night and it was just…kicking in. He had no way to tell.

“Woah, hey now, what’s wrong? You have to breathe, and crying isn’t the way to go…” Bill continued to stroke his Pine Tree’s back with one hand. With his other, he ran his fingers through Dipper’s fluffy brown locks and occasionally pulled on them, but very, very lightly, just to comfort the brunet more. He planted a kiss on his head, too.

“I…don’t know…but I-I have to ask…”

“Ask what? Well, actually, continue that after you stop crying. Just let it all out for now.”

Dipper hiccupped and whimpered as tears rolled down his cheeks. He tried to focus on just breathing and calming down, but he still really wanted to keep talking to Bill and confirm a few things. He felt a little better after a few minutes passed though. The room was just filled with comfortable silence the whole time, and Bill was caressing him very lovingly. It was always easy to relax in the demon’s touch, and resting his head on Bill’s chest while being held in his arms was pure bliss.

“…Did I make it up to you, Bill? I-I mean, um…a-are we…cool…? Do you forgive me for breaking my promise? I’m really sorry about that again, by the way…” he asked once he was a lot further away from passing out.

“Yes you did, Pine Tree, and yes, I forgive you. I don’t want you to break more promises, but I’d say sex wouldn’t have been as intense and enjoyable as it was tonight if you kept your word. You were so irresistible I gave in to all your requests; I’ll just do something about that whenever.”

“Thank you…s-so, you…you won’t leave me, right?”

“Of course not; you’re mine for all of eternity. I’ll never let anyone else have you.”

“Good…I really don’t wanna lose you…I-I was really scared…”

“Don’t be. I know what I said earlier, but I wouldn’t leave you because you can’t handle my rough treatment. I love you. Although it turns me on when you fear me, remember that after sex, alright? You’re my beloved Pine Tree,” Bill said in a gentle voice.

“I love you too…” Dipper replied, smiling.

“You know, I was planning to bite your neck all over and make it bleed a little as punishment, but any more than all I did and you would’ve passed out. How’s about I replace those bites with kisses and a few marks instead?”

“Of course. Anything you want, Bill.”

“Psh, I know you want it too. I’ll clean you up later.”

Dipper chuckled. “I do, and thanks. I probably can’t do it myself; my ass actually really hurts…You did a lot to it tonight.”

“Don’t worry, I won’t make you move too much.”

Bill started by kissing Dipper’s jawline, then proceeded to pepper his neck with lighter kisses. Once his lips were on the brunet’s shoulder, he licked his way back to his Pine Tree’s neck, causing Dipper to stifle a moan. The demon smirked, having felt the vibration on his tongue, but only for a brief moment. Eagerly, but not so harshly, he began to suck on Dipper’s skin. He kept at it for a while, making sure not to use his teeth. The rather lewd sounds that were being made from the golden-haired man passionately sucking on the brunet’s neck filled the room, which would turn Bill on, but he was too busy relishing his Pine Tree’s taste. The longer he took, the more he felt the urge to break Dipper’s skin though, so he pulled away before it could take over him.

“You’re beautiful, Pine Tree,” he said, admiring the mark he’d just made.

“So are you…which is why I have one last request for tonight. I know you don’t really like doing what I ask for when we’re—“

“We’re done with sex for the night, so I won’t mind. What can I do just for you, Pine Tree?”

“Can you kiss me, please? We uh…we’ve barely done that tonight, a-and I really enjoy it—I love kissing you. It’s really nice, e-especially when you…slip your tongue into me. A-And we usually do that before…Well, a-anyway, yeah, so…”

Bill chuckled, which would’ve made Dipper blush a little if he hadn’t already done much more embarrassing things that night.

“Anything for you, my beloved Pine Tree.”

**Author's Note:**

> Hello, I hope you guys enjoyed this fic! I hope the writing wasn't horrible, at least; it's been a while since I wrote smut. By a while, I mean since Christmas 2016 LOL


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